Phosphate → HCID 178462289, compound

HRID 382627Notes

Reaction equation

HRID 382627 reaction equation
[I-].[OH:2][C@@H:3]([C@H:5]1[C:33](=[O:34])[N:7]2[C:8]([C:20]([O:22]CC3C=CC([N+]([O-])=O)=CC=3)=[O:21])=[C:9]([C:11]3[S:15][C:14]4=[CH:16][N:17]([CH3:19])[CH:18]=[N+:13]4[CH:12]=3)[CH2:10][C@H:6]12)[CH3:4].P([O-])([O-])([O-])=O>C1COCC1.[Pd]>[OH:2][C@@H:3]([C@H:5]1[C:33](=[O:34])[N:7]2[C:8]([C:20]([O-:22])=[O:21])=[C:9]([C:11]3[S:15][C:14]4=[CH:16][N:17]([CH3:19])[CH:18]=[N+:13]4[CH:12]=3)[CH2:10][C@H:6]12)[CH3:4]

Participants

5

Reactant 2

HCID 1061PhosphateHCID 178462275HCID 178462275, compound

Product 1

HCID 178462289HCID 178462289, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 58 mg of 4-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(6-methylimidazo[5,1-b]thiazolium-2-yl)-1-carbapen-2-em-3-carboxylate iodide in 2 ml of THF and 2 ml of 1/15 M phosphate buffer (pH 6.8) was added 68 mg of 10% Pd-C. The reactor was purged with hydrogen, and the reaction mixture was stirred at room temperature for 4 hours. The catalyst was collected by filtration on Celite, and washed with water. The filtrate was washed with ethyl acetate, the aqueous layer was purified by column chromatography on DIAION HP-20 to give 5.4 mg of the title compound.

Workup

  1. customThe reactor was purged with hydrogen
  2. filtrationThe catalyst was collected by filtration on Celite
  3. washwashed with water
  4. washThe filtrate was washed with ethyl acetate
  5. customthe aqueous layer was purified by column chromatography on DIAION HP-20

Sources & evidence

ORD record
ord-e1314e589d174036858a74095fe5c9e0
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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